WO2020075509A1 - Composition de cristaux liquides polymérisable et élément d'affichage à cristaux liquides - Google Patents

Composition de cristaux liquides polymérisable et élément d'affichage à cristaux liquides Download PDF

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WO2020075509A1
WO2020075509A1 PCT/JP2019/037807 JP2019037807W WO2020075509A1 WO 2020075509 A1 WO2020075509 A1 WO 2020075509A1 JP 2019037807 W JP2019037807 W JP 2019037807W WO 2020075509 A1 WO2020075509 A1 WO 2020075509A1
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liquid crystal
mass
general formula
carbon atoms
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Japanese (ja)
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淳子 山本
雄一 井ノ上
純一 間宮
正臣 木村
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Dic株式会社
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Priority to JP2020524254A priority Critical patent/JP6844749B2/ja
Priority to CN201980051672.6A priority patent/CN112534022A/zh
Publication of WO2020075509A1 publication Critical patent/WO2020075509A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—Polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers

Definitions

  • the present invention relates to a liquid crystal composition containing a polymerizable compound and a liquid crystal display device using the same.
  • liquid crystal display devices such as liquid crystal panels and liquid crystal displays change the state of alignment of liquid crystal molecules by an external stimulus such as an electric field and use the resulting change in optical characteristics for display.
  • a liquid crystal display device has a structure in which liquid crystal molecules are filled in a gap between two transparent substrates, and liquid crystal molecules are arranged in a specific direction in advance on the surface of the substrate which is in contact with the liquid crystal molecules.
  • an alignment film is formed.
  • the production of a liquid crystal display device that does not require an alignment film was performed by injecting a liquid crystal compound, a polymerizable compound-containing liquid crystal composition containing a spontaneous alignment material and a polymerizable compound between the substrates, and applying a voltage to align the liquid crystal molecules.
  • the spontaneous alignment material and the polymerizable compound are polymerized to fix the alignment of the liquid crystal molecules.
  • the cause of image sticking which is a display failure of the liquid crystal display element, is due to impurities and a change in alignment of liquid crystal molecules (change in pretilt angle).
  • the image sticking caused by the change in the pretilt angle of the liquid crystal molecules changes the structure of the polymer when the same pattern is continuously displayed for a long time when the liquid crystal display element is configured, and as a result, the pretilt angle changes. It is a thing. Therefore, a polymerizable compound that forms a polymer having a rigid structure in which the polymer structure does not change is required.
  • the present invention suppresses a polymerizable compound that remains when a liquid crystal display device is formed without impeding the alignment regulating force for vertically aligning liquid crystal molecules, and is there a display defect due to a decrease in voltage holding ratio or a change in pretilt angle? Or to provide a liquid crystal composition containing an extremely small amount of a polymerizable compound, and to provide a liquid crystal display device using the same.
  • X i1 , X i2 , X i3 , X i4 , X i5 , X i6 , X i7 , X i8 , X i9 , X i10 , X i11 and X i12 each independently have 1 carbon atom.
  • R 21 , R 31 , R 41 , R 51 and R 61 each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
  • W is a single bond, —O— or methylene.
  • T represents a single bond or —COO—
  • p, t and q each independently represent 0, 1 or 2.
  • Sp i1 and Sp i2 each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one or two or more —CH 2 — in the alkylene group are directly adjacent to an oxygen atom.
  • L i1 and L i2 are each independently a single bond, —OCH 2 —, —CH 2 O—, —C 2 H 4 —, —OC 2 H 4 O—, —COO—, —OCO—, —.
  • the present invention provides a liquid crystal display device using the liquid crystal composition, an active matrix driving liquid crystal display device using the liquid crystal composition, a PSA mode, a PSVA mode, and a PS-IPS mode using the liquid crystal composition.
  • Another object is to provide a liquid crystal display element for PS-FSS mode and a liquid crystal display element in which an alignment film is not provided on the surface of at least one of a pair of substrates using the liquid crystal composition.
  • the liquid crystal display device produced by using the polymerizable liquid crystal composition of the present invention has a high voltage holding ratio (VHR) and is characterized in that the amount of unpolymerized polymerizable compound in the device is extremely small.
  • VHR voltage holding ratio
  • X i1 , X i2 , X i3 , X i4 , X i5 , X i6 , X i7 , X i8 , X i9 , X i10 , X i11 and X i12 are each independently. It represents an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom or a hydrogen atom.
  • the alkyl group and the alkoxy group are preferably linear, and a hydrogen atom, Methyl group, ethyl group, propyl group, methoxy group, ethoxy group, propoxy group, fluorine atom or chlorine atom is preferable, hydrogen atom, methyl group, ethyl group, methoxy group or fluorine atom is preferable, hydrogen atom, methyl group, methoxy Groups or fluorine atoms are preferred.
  • Two or more are preferably other than hydrogen atoms, two or three are preferably other than hydrogen atoms, and two are preferably other than hydrogen atoms.
  • the preferable number of carbon atoms of the alkyl group and the alkoxy group is preferably 10 to 18 when the orientation of the liquid crystal is important, and 1 to 4 is preferable when the solubility in the liquid crystal compound is important. Further, when importance is attached to tilt angle stability, an alkyl group is preferable. Further, the alkyl group and the alkoxy group may be linear or branched, but linear is particularly preferable.
  • Two or more of X i1 , X i2 , X i3 , X i4 , X i5 , X i6 , X i7 , X i8 , X i9 , X i10 , X i11 and X i12 are alkyl having 1 to 18 carbon atoms.
  • Group, an alkoxy group having 1 to 18 carbon atoms or a halogen atom is preferable, and the preferable number of carbon atoms of the alkyl group and the alkoxy group is 10 to 18 when the orientation of the liquid crystal is important. Is preferred, and 1 to 4 are preferred when importance is attached to the solubility in the liquid crystal compound. Further, when importance is attached to tilt angle stability, an alkyl group is preferable. Further, the alkyl group and the alkoxy group may be linear or branched, but linear is particularly preferable.
  • At least one of X i5 , X i6 , X i7, X i8 , X i9 , X i10 , X i11 and X i12 has 1 to 18 carbon atoms when the voltage holding ratio is important. It is preferably an alkyl group. The number of carbon atoms of the alkyl group is preferably 10 to 18 when the orientation of the liquid crystal is important, and 1 to 4 is preferable when the solubility in the liquid crystal compound is important. Further, when importance is attached to tilt stability, 1 to 3 is preferable.
  • the alkyl group may be linear or branched, but linear is particularly preferable.
  • At least one of X i5 , X i6 , X i7, X i8 , X i9 , X i10 , X i11, and X i12 is at least one.
  • a halogen atom is preferable, and fluorine is particularly preferable.
  • n i1 is 1, when emphasizing the tilt angle stability, X i5, X i6, X i7, and two are chosen from among X i8, 1 carbon atoms
  • X i5 is 1, when emphasizing the tilt angle stability, X i5, X i6, X i7, and two are chosen from among X i8, 1 carbon atoms
  • an alkyl group having 1 to 18 carbon atoms an alkoxy group having 1 to 18 carbon atoms, and a halogen atom are preferable, and an alkyl group having 1 to 3 carbon atoms and fluorine are particularly preferable.
  • L i1 and L i2 may be the same or different from each other, but it is more preferable that L i1 and L i2 are the same.
  • P i1 and P i2 each independently represent one of the following formulas (RI) to (R-IX).
  • R 21 , R 31 , R 41 , R 51 and R 61 are each independently of each other a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms.
  • a group, W is a single bond, -O- or a methylene group, T is a single bond or -COO-, and p, t and q are each independently 0, 1 or 2.
  • P i1 and P i2 are each independently a formula ( RI ), a formula (R-II), a formula (R-III), a formula (R-IV), Formula (RV) or formula (R-VII) is preferred, and formula (RI), formula (R-II), formula (R-III) or formula (R-IV) is preferred.
  • R 21 is a hydrogen atom in (RI)
  • R 21 is a methacryloxy group
  • R 21 is R 21 is It is more preferably a substituent group which is a methyl group), and more preferably a methacryloxy group.
  • Sp i1 and Sp i2 are preferably each independently a single bond or an alkylene group having 1 to 3 carbon atoms, and more preferably a single bond.
  • the polymerizable compound represented by the general formula (i) may be used alone or in combination of two or more.
  • the liquid crystal composition according to the present invention preferably contains 1 to 5 kinds of polymerizable compounds represented by the general formula (i), and 1 to 4 kinds of polymerizable compounds represented by the general formula (i). It is preferable to include a compound, and it is preferable to include one to three polymerizable compounds represented by the general formula (i).
  • the lower limit of the content of the polymerizable compound represented by the general formula (i) in the liquid crystal composition of the present invention is preferably 0.05% by mass, preferably 0.08% by mass, and preferably 0.1% by mass, 0.15 mass% is preferable, 0.17 mass% is preferable, 0.2 mass% is preferable, 0.22 mass% is preferable, 0.25 mass% is preferable, 0.27 mass% is preferable, and 0.
  • 3 mass% is preferable, 0.32 mass% is preferable, 0.35 mass% is preferable, 0.37 mass% is preferable, 0.4 mass% is preferable, 0.42 mass% is preferable, 0.45 mass% % Is preferred, 0.48% by mass is preferred, 0.5% by mass is preferred, 0.53% by mass is preferred, 0.55% by mass is preferred, 0.58% by mass is preferred, 0.60% by mass is Preferably, 0.63 mass% is preferable, 0.65 mass% is preferable, 0.68 mass% is preferable, 0.70 mass% is preferable, 0.73 mass% is preferable, 0.75 mass% is preferable, 0.78 mass% is preferable, and 0.8 Mass% is preferred.
  • the upper limit of the content of the polymerizable compound represented by the general formula (i) in the liquid crystal composition of the present invention is preferably 2.5% by mass, preferably 2.3% by mass, and preferably 2.1% by mass, 2 mass% is preferable, 1.8 mass% is preferable, 1.6 mass% is preferable, 1.5 mass% is preferable, 1 mass% is preferable, 0.95 mass% is preferable, and 0.9 mass% is.
  • 0.85 mass% is preferable
  • 0.8 mass% is preferable
  • 0.75 mass% is preferable
  • 0.7 mass% is preferable
  • 0.65 mass% is preferable
  • 0.6 mass% 0.55 mass% is preferable
  • 0.5 mass% is preferable
  • 0.45 mass% is preferable
  • 0.4 mass% is preferable.
  • the polymerizable compound represented by the general formula (i) When used alone, the smaller amount is preferable from the viewpoint of storage stability at low temperature, and a plurality of polymerizable compounds represented by the general formula (i) are combined. When used, a larger amount is preferable because the effect of the present application can be further exhibited.
  • the content of the polymerizable compound represented by the general formula (i) in the liquid crystal composition of the present invention is 0.1 to 1%. Is preferable, 0.2 to 0.8% is preferable, 0.3 to 0.75% is preferable, 0.35 to 0.7% is preferable, and 0.4 to 0.7% is preferable.
  • Suitable compounds of the polymerizable compound represented by the general formula (i) according to the present invention include the following formulas RM-1 to RM-33.
  • RM-1 to RM-33 are preferable, RM-3 to RM-11, RM-22 to RM-30 are more preferable, and RM-3, RM-11 and RM-25, RM-28 to RM-30. And are more preferable.
  • the liquid crystal composition according to the present invention contains the polymerizable compound represented by the general formula (i), but other polymerizable compounds may be used in combination.
  • the other polymerizable compound the following general formula (P) is used.
  • R p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms or —Sp p2 —P p2 , and one or more of the alkyl groups
  • One or more hydrogen atoms in the alkyl group may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom
  • P p1 and P p2 are each independently a general formula (P p1 -1) to a formula (P p1 -9)
  • R p11 and R p12 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms
  • W p11 represents a single bond
  • t p11 represents 0, 1, or 2.
  • Represents Ap1 , Ap2 and Ap3 are each independently (A p) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - may be replaced by -O-.)
  • (B p ) 1,4-phenylene group one —CH ⁇ present in this group or two or more —CH ⁇ which are not adjacent to each other may be replaced with —N ⁇ ) and (c).
  • m p1 represents 0, 1, 2 or 3 and when a plurality of Z p1 , A p2 , Sp p2 and / or P p2 are present in the molecule, they may be the same or different, A p3 represents a single bond when m p1 is 0 and A p1 is a phenanthrene-2,7-diyl group or an anthracene-2,6-diyl group.
  • the compound represented by the general formula (i) is excluded.
  • Compounds represented by are preferred. Moreover, it is preferable to contain 1 type or 2 types or more of the said polymerizable monomer.
  • R p1 is preferably -Sp p2 -P p2 .
  • P p1 and P p2 are preferably each independently any of formulas (P p1 -1) to (P p1 -3), and more preferably (P p1 -1).
  • R p11 and R p12 are each independently a hydrogen atom or a methyl group.
  • 0 or 1 is preferable for tp11 .
  • W p11 is preferably a single bond, a methylene group or an ethylene group.
  • m p1 is preferably 0, 1 or 2, and more preferably 0 or 1.
  • Z p1 and Z p2 are each independently a single bond, —OCH 2 —, —CH 2 O—, —CO—, —C 2 H 4 —, —COO—, —OCO—, —COOC 2 H 4 —.
  • a p1 , A p2 and A p3 are each independently preferably a 1,4-phenylene group or a 1,4-cyclohexylene group, and more preferably a 1,4-phenylene group.
  • the 1,4-phenylene group is preferably substituted with one fluorine atom, one methyl group or one methoxy group in order to improve the compatibility with the liquid crystal compound.
  • the total content of the compound represented by the general formula (P) is preferably 0.05 to 10% with respect to the composition containing the compound represented by the general formula (P) of the present application, Preferably, it contains 0.1 to 8%, preferably 0.1 to 5%, more preferably 0.1 to 3%, and 0.2 to 2%. Preferably, it contains 0.2 to 1.3%, more preferably 0.2 to 1%, and more preferably 0.2 to 0.56%.
  • the preferable lower limit of the total content of the compound represented by the general formula (P) is 0.01% with respect to the composition containing the compound represented by the general formula (P) of the present application, and is 0.1%. 03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3% %.
  • a preferred upper limit of the total content of the compound represented by the general formula (P) is 10% and 8% with respect to the composition containing the compound represented by the general formula (P) of the present application. 5%, 3%, 1.5%, 1.2%, 1%, 0.8%, and 0.5%.
  • the content is small, the effect of adding the compound represented by the general formula (P) is difficult to appear, and problems such as weak alignment control force of the liquid crystal composition or weakening over time occur. Problems such as an increase in the amount remaining afterward, a long time for curing, and a decrease in the reliability of the liquid crystal occur. Therefore, the content is set in consideration of these balances.
  • Preferred examples of the compound represented by the general formula (P) according to the present invention include polymerizable compounds represented by the following formulas (P-1-1) to (P-1-46).
  • P p11, P p12, Sp p11 and Sp p12 are the same as defined P p11, P p12, Sp p11 and Sp p12 in the general formula (P-1).
  • Preferred examples of the compound represented by the general formula (P) according to the present invention include polymerizable compounds represented by the following formulas (P-2-1) to (P-2-12).
  • Preferred examples of the compound represented by the general formula (P) according to the present invention include polymerizable compounds represented by the following formulas (P-3-1) to (P-3-15).
  • Preferred examples of the compound represented by the general formula (P) according to the present invention include polymerizable compounds represented by the following formulas (P-4-1) to (P-4-15).
  • the liquid crystal composition according to the present invention has 1 to 3 kinds of polymerizable compounds represented by the general formula (i) and 1 to 3 kinds of general formulas (P) having different structures from those of the general formula (i). ) Can be included in the polymerizable compound.
  • the lower limit of the total content of the compound represented by the general formula (i) and the polymerizable compound represented by the general formula (P) is preferably 0.01% by mass in the general formula (i), and 0.03% by mass.
  • 0.2 mass% is preferable, 0.22 mass% is preferable, 0.25 mass% is preferable, 0.27 mass% is preferable, 0.3 mass% is preferable, 0.32 mass% is preferable, 0.35 mass% is preferable, 0.37 mass% is preferable, and 0.4 mass% is preferable.
  • the upper limit of the total content of the polymerizable compound represented by the general formula (i) and the polymerizable compound represented by the general formula (P) in the liquid crystal composition of the present invention is preferably 2.0% by mass. 0.8 mass% is preferable, 1.5 mass% is preferable, 1.0 mass% is preferable, 0.8 mass% is preferable, 0.5 mass% is preferable, 0.47 mass% is preferable, and 0.1 mass% is.
  • Mass% is preferable, 0.45 mass% is preferable, 0.43 mass% is preferable, 0.40 mass% is preferable, 0.37 mass% is preferable, 0.35 mass% is preferable, 0.32 mass% Is preferable, 0.30 mass% is preferable, 0.27 mass% is preferable, 0.25 mass% is preferable, 0.23 mass% is preferable, and 0.20 mass% is preferable.
  • the liquid crystal composition may further contain liquid crystal molecules and an alignment aid having a function of spontaneously aligning the liquid crystal molecules and having an adsorption group (polar group).
  • an alignment aid having a function of spontaneously aligning the liquid crystal molecules and having an adsorption group (polar group).
  • the alignment aid is a member (electrode (for example, ITO)), substrate (for example, glass substrate, acrylic substrate, transparent substrate, flexible substrate, or the like) that directly contacts the liquid crystal layer containing the liquid crystal composition, resin.
  • electrode for example, ITO
  • substrate for example, glass substrate, acrylic substrate, transparent substrate, flexible substrate, or the like
  • ITO electrode
  • substrate for example, glass substrate, acrylic substrate, transparent substrate, flexible substrate, or the like
  • insulating films for example, inorganic material films, SiNx, etc.
  • the alignment aid induces alignment of the liquid crystal molecules, a polymerizable group for polymerization, a mesogenic group similar to the liquid crystal molecules, an adsorption group (polar group) capable of interacting with a member that directly contacts the liquid crystal layer. It is preferable to have an orientation-inducing group.
  • the adsorption group and the orientation-inducing group are bonded to the mesogen group, and the polymerizable group is substituted for the mesogen group, the adsorption group and the orientation-inducing group directly or via a spacer group as necessary.
  • the polymerizable group is preferably substituted with the mesogen group in a state of being incorporated in the adsorptive group.
  • orientation-inducing group has a function of inducing the orientation of liquid crystal molecules, and is preferably a group represented by the following general formula (AK).
  • R AK1 represents a linear or branched alkyl group having 1 to 20 carbon atoms. However, one or more —CH 2 — in the alkyl group do not have an oxygen atom directly bonded and are independently —CH ⁇ CH—, —C ⁇ C—, —O—, — It may be substituted with CO—, —COO— or —OCO—, and one or more hydrogen atoms in the alkyl group may be independently substituted with a halogeno group.
  • R AK1 is preferably a linear or branched alkyl group having 1 to 20 carbon atoms, more preferably a linear alkyl group having 1 to 20 carbon atoms, and more preferably a linear alkyl group. It is more preferable to represent an alkyl group having 1 to 8 carbon atoms.
  • one or two or more non-adjacent —CH 2 — groups in the alkyl group are independently —CH ⁇ CH—, —C ⁇ C—, —O—, —CO—, —COO— or It may be substituted with —OCO—.
  • the hydrogen atom in the alkyl group may be substituted with a fluorine atom or a chlorine atom, or may be substituted with a fluorine atom.
  • the above alignment inducing group is bonded to a mesogenic group.
  • Polymerizable group Polymerizable group, P AP1 -Sp AP1 - is preferably represented by.
  • P AP1 is preferably a group selected from the group represented by the following general formulas (AP-1) to (AP-9).
  • R AP1 and R AP2 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 10 carbon atoms.
  • one or two or more —CH 2 — in the alkyl group may be substituted with —O— or —CO—, and one or two or more hydrogen atoms in the alkyl group are each independently. Then, it may be substituted with a halogen atom or a hydroxyl group.
  • W AP1 represents a single bond, —O—, —COO— or —CH 2 —.
  • t AP1 represents 0, 1 or 2.
  • P AP1 is preferably a group represented by the following general formula (AP-1) to general formula (AP-7), and is represented by the following general formula (AP-1) or general formula (AP-2). Group represented by formula (AP-1) is more preferable.
  • Sp AP1 is preferably a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, and more preferably a single bond or a linear alkylene group having 1 to 20 carbon atoms. It is more preferable to represent a single bond or a linear alkylene group having 2 to 10 carbon atoms.
  • one or two or more non-adjacent —CH 2 — groups in the alkylene group are independently —CH ⁇ CH—, —C ⁇ C—, —O—, —CO—, It may be substituted with —COO— or —OCO—.
  • the hydrogen atom in P AP1- Sp AP1- may be substituted with a polymerizable group, an adsorptive group and / or an orientation-inducing group.
  • Polymerizable group (P AP1 -Sp AP1 -), the polymerizable group, mesogen group may be bonded to an adsorptive group and / or orientation-induced group.
  • the polymerizable group (P AP1 -Sp AP1 -) is preferably binding to the mesogenic groups, the adsorption group or orientation-induced group, and more preferably binding to the mesogenic groups or adsorptive groups.
  • P AP1 and / or Sp AP1 ⁇ molecules may be the same or different from each other.
  • the mesogen group means a group having a rigid portion, for example, a group having at least one cyclic group, preferably a group having 2 to 4 cyclic groups, and 3 to 4 cyclic groups. The groups provided are more preferred. In addition, if necessary, the cyclic group may be linked by a linking group.
  • the mesogen group preferably has a skeleton similar to that of liquid crystal molecules (liquid crystal compound) used in the liquid crystal layer.
  • cyclic group refers to an atomic group in which constituent atoms are cyclically bonded, and is a carbon ring, a heterocyclic ring, a saturated or unsaturated cyclic structure, a monocyclic or bicyclic structure, Including polycyclic structures, aromatic and non-aromatic.
  • the cyclic group may contain at least one hetero atom, and may be further substituted with at least one substituent (halogeno group, polymerizable group, organic group (alkyl, alkoxy, aryl, etc.)).
  • substituent halogeno group, polymerizable group, organic group (alkyl, alkoxy, aryl, etc.)
  • the mesogenic group preferably contains two or more single rings.
  • the mesogen group is preferably represented, for example, by the general formula (AL).
  • a AL1 and A AL2 each independently represent a divalent cyclic group.
  • One or more hydrogen atoms in Z AL1 , A AL1 and A AL2 may be independently substituted with a halogeno group, an adsorbing group, P AP1- Sp AP1 -or a monovalent organic group.
  • a plurality of Z AL1 and A AL1 are present in the molecule, they may be the same or different from each other.
  • n AL1 represents an integer of 1 to 5.
  • Z AL1 is preferably a single bond or an alkylene group having 2 to 20 carbon atoms, more preferably a single bond or an alkylene group having 2 to 10 carbon atoms, and a single bond is preferable. , — (CH 2 ) 2 — or — (CH 2 ) 4 —.
  • One or two or more non-adjacent —CH 2 — in the alkylene group may be substituted with —O—, —COO—, or —OCO—.
  • Z AL1 is a single bond in which rings are directly connected to each other or an even number of atoms directly connecting the rings is even.
  • the form is preferred. For example, in the case of —CH 2 —CH 2 COO—, the number of atoms directly connecting the rings is four.
  • a AL1 and A AL2 each independently represent a divalent cyclic group.
  • the divalent cyclic group include 1,4-phenylene group, 1,4-cyclohexylene group, 1,4-cyclohexenyl group, tetrahydropyran-2,5-diyl group, 1,3-dioxane-2, 5-diyl group, tetrahydrothiopyran-2,5-diyl group, thiophene-2,5-diyl group, 1,4-bicyclo (2.2.2) octylene group, decahydronaphthalene-2,6-diyl group , Pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene-2,5-diyl group-, 1,2,3,4-tetrahydronaphthalene-2 , 6-diyl group,
  • the substituent is preferably a fluorine atom or an alkyl group having 1 to 8 carbon atoms. Further, the alkyl group may be substituted with a fluorine atom or a hydroxyl group.
  • one or more hydrogen atoms in the cyclic group may be substituted with a halogeno group, an adsorptive group, P AP1- Sp AP1 -or a monovalent organic group.
  • the monovalent organic group is a group having a chemical structure formed by converting an organic compound into a monovalent group, and is obtained by removing one hydrogen atom from the organic compound. Refers to an atomic group.
  • Examples of such a monovalent organic group include an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, and an alkenyloxy group having 2 to 15 carbon atoms. And an alkyl group having 1 to 15 carbon atoms or an alkoxy group having 1 to 14 carbon atoms, preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.
  • an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms and more preferably an alkyl group having 1 to 3 carbon atoms or an alkyl group having 1 to 2 carbon atoms.
  • An alkoxy group is particularly preferred, and an alkyl group having 1 or 2 carbon atoms or an alkoxy group having 1 carbon atom is most preferred.
  • one or two or more non-adjacent —CH 2 — in the above alkyl group, alkenyl group, alkoxy group and alkenyloxy group may be substituted with —O—, —COO— or —OCO—.
  • the monovalent organic group may have a role as an orientation inducing group described later.
  • m AL1 is preferably an integer of 1 to 4, more preferably an integer of 1 to 3, and even more preferably 2 or 3.
  • the general formula (AL) is a structure in which two hydrogen atoms are eliminated from these compounds.
  • one or more hydrogen atoms in the cyclohexane ring, benzene ring or naphthalene ring are each independently a halogeno group
  • P AP1 -Sp AP1 -It may be substituted with a monovalent organic group (for example, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms), an adsorption group or an orientation inducing group.
  • formulas (me-8) to (me-44) preferred forms are formulas (me-8) to (me-44), and more preferred forms are formulas (me-8) to (me-10) and formulas (me-12) to (Me-18), formulas (me-22) to (me-24), formulas (me-26) to (me-27) and formulas (me-29) to (me-44), and more preferable forms Are expressions (me-12), (me-15) to (me-16), (me-22) to (me-24), (me-29), (me-34), (me-36) To (me-37) and (me-42) to (me-44).
  • a particularly preferred form is the following general formula (AL-1) or (AL-2), and a most preferred form is the following general formula (AL-1).
  • X AL101 to X AL118 and X AL201 to X AL214 each independently represent a hydrogen atom, a halogeno group, P AP1- Sp AP1- , an adsorption group or an orientation-inducing group.
  • Ring A AL11, Ring A AL12 and ring A AL21 each independently represent a cyclohexane ring or a benzene ring.
  • Any one type or two or more types of X AL101 to X AL118 and X AL201 to X AL214 are substituted with an adsorption group.
  • Any one type or two or more types of X AL101 to X AL118 and X AL201 to X AL214 are substituted with an orientation-inducing group.
  • P AP1 -Sp AP1 - may be substituted with.
  • the general formula (AL-1) or the general formula (AL-2) has one or more kinds of P AP1 -Sp APl- in its molecule.
  • X AL101 is preferably an orientation-inducing group.
  • At least one of X AL109 , X AL110 and X AL111 is preferably an adsorption group, and both X AL109 and X AL110 are adsorption groups or X AL110 is an adsorption group. Is more preferable, and X AL110 is even more preferably an adsorptive group.
  • X AL109 , X AL110 and X AL111 is P AP1 —Sp AP1 ⁇ or an adsorption group having a polymerizable site in the structure, and X AL109 and X AL111 more preferably - one or both of P AP1 -Sp AP1.
  • one or two of X AL104 to X AL108 and X AL112 to X AL116 are independently an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms. Alternatively, it is preferably a halogeno group, and more preferably an alkyl group having 1 to 3 carbon atoms or a fluorine atom. In particular, it is preferable that X AL105 , X AL106, and X AL107 are each independently an alkyl group having 1 to 3 carbon atoms or a fluorine atom.
  • X AL201 is preferably an orientation-inducing group.
  • At least one of X AL207 , X AL208 and X AL209 is preferably an adsorptive group, and both X AL207 and X AL208 are adsorptive groups or X AL208 is an adsorptive group. Is more preferable, and X AL208 is even more preferably an adsorptive group.
  • At least one of X AL207 , X AL208 and X AL209 is preferably P AP1 -Sp AP1 -or an adsorbing group having a polymerizable site in the structure, and X AL207 and X AL209 more preferably - one or both of P AP1 -Sp AP1.
  • one or two of X AL202 to X AL206 and X AL210 to X AL214 are independently an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms. Alternatively, it is preferably a halogeno group, and more preferably an alkyl group having 1 to 3 carbon atoms or a fluorine atom.
  • X AL204, X AL205 or X AL206 are each independently preferably an alkyl group or a fluorine atom of 1 to 3 carbon atoms.
  • the adsorptive group is a group having a role of adsorbing an adsorbent which is a layer that comes into contact with the liquid crystal composition such as a substrate, a film and an electrode.
  • Adsorption is generally classified into chemisorption in which a chemical bond (covalent bond, ionic bond, or metal bond) is created and adsorbed between an adsorbent and an adsorbate, and physical adsorption other than chemisorption.
  • the adsorption may be either chemical adsorption or physical adsorption, but physical adsorption is preferable. Therefore, the adsorbing group is preferably a group capable of physically adsorbing to the adsorbent, and more preferably a group capable of bonding to the adsorbent by intermolecular force.
  • Examples of the form of bonding with an adsorbent by an intermolecular force include forms by interaction such as permanent dipole, permanent quadrupole, dispersion force, charge transfer force, and hydrogen bond.
  • a preferred form of the adsorptive group is a form that can be bonded to the adsorbent by hydrogen bonding.
  • the adsorptive group may serve as either a donor or an acceptor of a proton via a hydrogen bond, or may serve as both.
  • the adsorbing group is preferably a group including a polar element having an atomic group in which a carbon atom and a hetero atom are linked (hereinafter, the “adsorbing group” is also referred to as a “polar group”).
  • a polar element refers to an atomic group in which a carbon atom and a hetero atom are directly connected.
  • the heteroatom is preferably at least one selected from the group consisting of N, O, S, P, B and Si, and is at least one selected from the group consisting of N, O and S Is more preferable, at least one selected from the group consisting of N and O is more preferable, and O is particularly preferable.
  • the valence of the polar element is not particularly limited, such as monovalent, divalent, or trivalent, and the number of polar elements in the adsorptive group is not particularly limited.
  • the orientation aid preferably has 1 to 8 adsorption groups in one molecule, more preferably 1 to 4 adsorption groups, and further preferably 1 to 3 adsorption groups.
  • a hydrogen atom is P AP1 -Sp AP1 in adsorptive group - substituted with structural and P AP1 -Sp AP1 - hydrogen atoms in the -OH
  • the structure substituted with is included in the adsorption group.
  • Adsorption group contains one or more polar elements and is roughly classified into cyclic group type and chain type.
  • the cyclic base type is a form including a cyclic group having a cyclic structure containing a polar element in its structure, and the chain base form is a cyclic group having a cyclic structure containing a polar element in its structure. Is not included.
  • the -chain type is a form having a polar element in a linear or branched chain group, and may have a cyclic structure containing no polar element in a part thereof.
  • a cyclic group-type adsorptive group means a form having a structure containing at least one polar element in a cyclic atomic arrangement.
  • the cyclic group is as described above. Therefore, the cyclic group type adsorptive group only needs to contain a cyclic group containing a polar element, and the entire adsorptive group may be branched or linear.
  • a chain-type adsorptive group refers to a structure in which a molecule does not include a cyclic atomic arrangement including a polar element, and includes at least one polar element in a linear atomic arrangement (which may be branched). Means a form having
  • a chain group refers to an atomic group in which a structural atom does not include a cyclic atom arrangement, and constituent atoms are linearly (may be branched), and an acyclic group. Group.
  • the chain group refers to a linear or branched aliphatic group, and may contain either a saturated bond or an unsaturated bond.
  • open-chain groups include, for example, alkyl, alkenyl, alkoxy, ester, ether or ketone.
  • the hydrogen atom in these groups may be substituted with at least one substituent (a reactive functional group (such as a vinyl group, an acryl group, or a methacryl group) or a chain organic group (such as an alkyl group or a cyano group)).
  • a reactive functional group such as a vinyl group, an acryl group, or a methacryl group
  • a chain organic group such as an alkyl group or a cyano group
  • the cyclic group type adsorptive group may be a heteroaromatic group having 3 to 20 carbon atoms (including a condensed ring) or a heteroalicyclic group having 3 to 20 carbon atoms (including a condensed ring). More preferably, it is a heteroaromatic group having 3 to 12 carbon atoms (including a condensed ring) or a heteroalicyclic group having 3 to 12 carbon atoms (including a condensed ring), more preferably a 5-membered heterocyclic group. More preferably, they are an aromatic group, a 5-membered heteroalicyclic group, a 6-membered heteroaromatic group, or a 6-membered heteroalicyclic group.
  • the hydrogen atom in these ring structures may be substituted with a halogeno group, a linear or branched alkyl group having 1 to 5 carbon atoms or an alkyloxy group.
  • the chain type adsorptive group is preferably a linear or branched alkyl group having 1 to 20 carbon atoms in which a hydrogen atom or —CH 2 — in the structure is substituted with a polar element.
  • One or two or more non-adjacent —CH 2 — groups in the alkyl group are —CH ⁇ CH—, —C ⁇ C—, —O—, —CO—, —COO—, —OCO— or —. It may be substituted with OCO-COO-.
  • the chain-type adsorptive group preferably contains one or more polar elements at the end thereof.
  • the hydrogen atom in the adsorptive group may be replaced by a polymerizable group.
  • the polar element examples include a polar element containing an oxygen atom (hereinafter, oxygen-containing polar element), a polar element containing a nitrogen atom (hereinafter, nitrogen-containing polar element), and a polar element containing a phosphorus atom (hereinafter, phosphorus-containing polarity). Element), a polar element containing a boron atom (hereinafter, a boron-containing polar element), a polar element containing a silicon atom (hereinafter, a silicon-containing polar element), or a polar element containing a sulfur atom (hereinafter, a sulfur-containing polar element). . From the viewpoint of the adsorption ability, the polar element is preferably a nitrogen-containing polar element, a nitrogen-containing polar element, or an oxygen-containing polar element, and more preferably an oxygen-containing polar element.
  • oxygen-containing polar element at least one group selected from the group consisting of a hydroxyl group, an alkylol group, an alkoxy group, a formyl group, a carboxyl group, an ether group, a carbonyl group, a carbonate group and an ester group, It is preferably a group linked to an atom.
  • nitrogen-containing polar element examples include at least one group selected from the group consisting of a cyano group, a primary amino group, a secondary amino group, a tertiary amino group, a pyridyl group, a carbamoyl group, and a ureido group, It is preferably a group linked to an atom.
  • the phosphorus-containing polar element is preferably at least one group selected from the group consisting of a phosphinyl group and a phosphate group or a group in which the group is linked to a carbon atom.
  • a cyclic group having an oxygen-containing polar element hereinafter, oxygen-containing cyclic group
  • a cyclic group having a nitrogen-containing polar element hereinafter, nitrogen-containing cyclic group
  • a sulfur-containing polar group Cyclic group with an element hereinafter, sulfur-containing cyclic group
  • a chain group with an oxygen-containing polar element hereinafter, oxygen-containing chain group
  • a chain group with a nitrogen-containing polar element hereinafter, One or more groups selected from the group consisting of a nitrogen-containing chain group
  • an oxygen-containing cyclic group, a sulfur-containing cyclic group, and oxygen-containing More preferably, it contains one or more groups selected from the group consisting of a chain type group and a nitrogen-containing chain type group.
  • the oxygen-containing cyclic group preferably contains any of the following groups having an oxygen atom as an ether group in the ring structure.
  • the oxygen-containing cyclic group preferably includes any of the following groups having an oxygen atom as a carbonyl group, a carbonate group, or an ester group in the ring structure.
  • the nitrogen-containing cyclic group preferably contains any of the following groups.
  • the oxygen-containing group preferably contains any of the following groups.
  • R at1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • Z at1 represents a single bond, a linear or branched alkylene group having 1 to 15 carbon atoms, or a linear or branched alkenylene group having 2 to 18 carbon atoms.
  • —CH 2 — in the alkylene group or alkenylene group may be substituted with —O—, —COO—, —C ( ⁇ O) —, or —OCO— so that oxygen atoms are not directly adjacent to each other.
  • the nitrogen-containing chain-type group preferably contains any of the following groups.
  • R at , R bt , R ct and R dt each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • the adsorbing group is preferably a group represented by the following general formula (AT).
  • Sp AT1 represents a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms.
  • W AT1 represents a single bond or the following general formula (WAT1) or (WAT2).
  • Z AT1 represents a monovalent group containing a polar element.
  • the hydrogen atom in Z AT1 may be replaced with —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —.
  • Sp WAT1 and Sp WAT2 each independently represent a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms, and the hydrogen atom in the alkylene group is —OH, — CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 — may be substituted, and —CH 2 — in the alkylene group is a cyclic group, —O— so that an oxygen atom is not directly bonded.
  • Sp AT1 , Sp WAT1 and Sp WAT2 each independently represent a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, and a single bond or a linear carbon atom number. It is more preferable to represent an alkylene group having 1 to 20 carbon atoms, and it is more preferable to represent a single bond or a linear alkylene group having 2 to 10 carbon atoms.
  • one or two or more non-adjacent —CH 2 — in the alkylene group are independently —CH ⁇ CH so that an oxygen atom is not directly bonded. It may be substituted with-, -C ⁇ C-, -O-, -CO-, -COO- or -OCO-.
  • the hydrogen atoms in Sp AT1 and Sp WAT1 may be independently substituted with —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —.
  • Z AT1 represents a monovalent group containing a polar element and is preferably a group represented by the following general formula (ZAT1-1) or (ZAT1-2).
  • Sp ZAT11 and Sp ZAT12 each independently represent a linear or branched alkylene group having 1 to 25 carbon atoms.
  • the hydrogen atom in the alkylene group may be substituted with —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —, and —CH 2 — in the alkylene group is oxygen. It may be substituted with a cyclic group, —O—, —COO—, —C ( ⁇ O) —, —OCO— or —CH ⁇ CH— so that the atoms are not directly adjacent.
  • Z ZAT11 represents a group containing a polar element.
  • the structure represented by the ring containing Z ZAT12 in the general formula (ZAT1-2) represents a 5- to 7-membered ring.
  • the hydrogen atom in Z ZAT11 and Z ZAT12 may be substituted with —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —.
  • R ZAT11 and R ZAT12 each independently represent a linear or branched alkyl group having 1 to 8 carbon atoms.
  • the hydrogen atom in the alkyl group may be replaced by —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —, and —CH 2 — in the alkyl group is oxygen. It may be substituted with a cyclic group, —O—, —COO—, —C ( ⁇ O) —, —OCO— or —CH ⁇ CH— so that the atoms are not directly bonded.
  • the group represented by the general formula (ZAT1-1) is preferably a group represented by the following general formulas (ZAT1-1-1) to (ZAT1-1-30).
  • the hydrogen atom bonded to the carbon atom may be substituted with —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —.
  • Sp ZAT11 represents a linear or branched alkylene group having 1 to 25 carbon atoms.
  • the hydrogen atom in the alkylene group may be substituted with —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —, and —CH 2 — in the alkylene group is oxygen. It may be substituted with a cyclic group, —O—, —COO—, —C ( ⁇ O) —, —OCO— or —CH ⁇ CH— so that the atoms are not directly adjacent.
  • R ZAT11 represents a linear or branched alkyl group having 1 to 8 carbon atoms.
  • the hydrogen atom in the alkyl group may be replaced by —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —, and —CH 2 — in the alkyl group is oxygen. It may be substituted with a cyclic group, —O—, —COO—, —C ( ⁇ O) —, —OCO— or —CH ⁇ CH— so that the atoms are not directly bonded.
  • the group represented by the general formula (ZAT1-2) is preferably a group represented by the following general formulas (ZAT1-2-1) to (ZAT1-2-9).
  • the hydrogen atom bonded to the carbon atom may be substituted with a halogen atom, —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —.
  • Sp ZAT11 represents a linear or branched alkylene group having 1 to 25 carbon atoms.
  • the hydrogen atom in the alkylene group may be substituted with —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —, and —CH 2 — in the alkylene group is oxygen. It may be substituted with a cyclic group, —O—, —COO—, —C ( ⁇ O) —, —OCO— or —CH ⁇ CH— so that the atoms are not directly adjacent.
  • Examples of the group represented by the general formula (ZAT1-1) include the following groups.
  • R tc represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or P AP1 —Sp AP1 —.
  • the hydrogen atom in the alkyl group may be replaced by —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —, and —CH 2 — in the alkyl group is oxygen. It may be substituted with a cyclic group, —O—, —COO—, —C ( ⁇ O) —, —OCO— or —CH ⁇ CH— so that the atoms are not directly adjacent.
  • P AP1 -Sp AP1 - may be substituted with.
  • the orientation aid is preferably in a form in which the polar element contained in the adsorptive group or the polar element contained in the polymerizable group is localized.
  • the adsorptive group is an important structure for vertically aligning liquid crystal molecules, and when the adsorptive group and the polymerizable group are adjacent to each other, a better alignment property can be obtained, and a favorable liquid crystal composition can be obtained. Shows solubility.
  • the orientation aid preferably has a form having a polymerizable group and an adsorptive group on the same ring of the mesogen group.
  • one or more polymerizable groups and one or more adsorbing groups are respectively bonded on the same ring, and at least one of the one or more polymerizable groups or at least one of the one or more adsorbing groups.
  • a form in which one is bonded to the other and has a polymerizable group and an adsorptive group on the same ring is included.
  • a hydrogen atom in the spacer group of the polymerizable group may be replaced with an adsorptive group, and further, a hydrogen atom in the adsorptive group may be replaced with a polymerizable group through the spacer group. Good.
  • the orientation aid is preferably a compound represented by the following general formula (SAL).
  • the hydrogen atom bonded to the carbon atom is a linear or branched alkyl group having 1 to 25 carbon atoms, —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1. It may be replaced with-. However, the hydrogen atom in the alkyl group may be replaced by —OH, —CN, —Sp AT1 —W AT1 —Z AT1 or P AP1 —Sp AP1 —, and —CH 2 — in the alkyl group is oxygen. It may be substituted with a cyclic group, —O—, —COO—, —C ( ⁇ O) —, —OCO— or —CH ⁇ CH— so that the atoms are not directly bonded.
  • R AK1 has the same meaning as R AK1 in formula (AK).
  • a AL1 and A AL2 each independently have the same meaning as A AL1 and A AL2 in formula (AL).
  • Z AL1 has the same meaning as Z AL1 in formula (AL).
  • n AL1 has the same meaning as m AL1 in formula (AL).
  • Sp AT1 has the same meaning as Sp AT1 in formula (AT).
  • W AT1 has the same meaning as W AT1 in formula (AT).
  • Z AT1 has the same meaning as Z AT1 in formula (AT).
  • the compound represented by the general formula (SAL) is preferably a compound represented by the following formulas (SAL-1.1) to (SAL-2.9).
  • the amount of the alignment aid contained in the liquid crystal composition is preferably about 0.01 to 50% by mass.
  • the more preferable lower limit values thereof are 0.05% by mass and 0.1% by mass from the viewpoint of aligning the liquid crystal molecules more preferably.
  • the more preferable upper limit values thereof are 30% by mass, 10% by mass, 7% by mass, 5% by mass, 4% by mass and 3% by mass from the viewpoint of improving response characteristics.
  • the total content of the liquid crystal composition is preferably 0.05 to 10% by mass, preferably 0.1 to 8% by mass, and 0.1 to 5% by mass. Preferably, it is 0.1 to 3% by mass, preferably 0.2 to 2% by mass, more preferably 0.2 to 1.3% by mass, and 0.2 to 1% by mass. And preferably 0.2 to 0.56% by mass.
  • the polymerizable liquid crystal composition of the present invention contains a compound represented by the general formula (i) as a polymerizable compound, and further contains a compound represented by the general formula (SAL) (that is, contains an adsorption group Z AT1) . It is preferable to contain a compound represented by the formula (P) and an alignment aid which is a compound.
  • the compound represented by the general formula (SAL), which is an alignment aid, has a function of aligning the liquid crystal compound in the liquid phase composition substantially perpendicularly to the substrate, and is represented by the general formula (i).
  • the compound represented and the compound represented by the general formula (P) are used for stabilizing the alignment in which the liquid crystal compound is tilted in a certain direction with respect to the substrate in the state where no voltage is applied. Stabilization of the tilt of the liquid crystal compound with respect to the substrate can be achieved to a certain extent by using only the compound represented by the general formula (P), but the compound represented by the general formula (i) is used. As a result, the problem to be solved by the present application can be achieved.
  • the preferred lower limit of the total content is 0.01% by mass, 0.03% by mass, 0.05% by mass, 0.08% by mass, and 0% by mass with respect to the liquid crystal composition. 0.1% by mass, 0.15% by mass, 0.2% by mass, 0.25% by mass, and 0.3% by mass.
  • a preferable upper limit value of the total content of the compound represented by the general formula (SAL) and the compound represented by the general formula (P) is 10% by mass, and 8% by mass with respect to the liquid crystal composition. Yes, 5% by mass, 3% by mass, 1.5% by mass, 1.2% by mass, 1% by mass, 0.8% by mass, 0.5% by mass is there.
  • SAL a compound represented by the general formula
  • P a compound represented by the general formula (P)
  • the total content of the compound represented by the general formula (SAL) and the compound represented by the general formula (P) is too large, the compound may remain after curing depending on, for example, the illuminance of active energy rays. In some cases, problems such as an increase in the amount to be applied, a long time for curing, and a decrease in reliability of the liquid crystal composition may occur. Therefore, it is preferable to set the contents of these in consideration of these balances.
  • the liquid crystal composition of the present invention contains a compound selected from the group consisting of compounds represented by general formulas (N-01), (N-02), (N-03), (N-04) and (N-05). It is preferable to contain one kind or two or more kinds. These compounds correspond to compounds having a negative dielectric anisotropy.
  • the “compound having negative dielectric anisotropy” refers to a compound having a negative ⁇ sign and an absolute value larger than 2.
  • ⁇ of the compound is a value extrapolated from the measured value of the dielectric anisotropy of the composition obtained by adding the compound to a composition that is dielectrically almost neutral at 25 ° C.
  • the liquid crystal composition of the present invention contains one or more compounds selected from the group of compounds represented by formulas (N-01), (N-02), (N-03) and (N-04). It is preferable to contain.
  • R 21 and R 22 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or 2 carbon atoms.
  • 8 represents an alkenyloxy group, and one or two or more non-adjacent —CH 2 — groups in each group independently represent —CH ⁇ CH—, —C ⁇ C—, —O—, —CO. It may be substituted with —, —COO— or —OCO—, and each Z 1 independently represents a single bond, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —COO—. , —OCO—, —OCF 2 —, —CF 2 O—, —CH ⁇ CH—, —CF ⁇ CF— or —C ⁇ C—, and m independently represents 1 or 2.
  • R 21 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and further preferably an alkyl group having 1 to 4 carbon atoms. However, when Z 1 is other than a single bond, R 21 is preferably an alkyl group having 1 to 3 carbon atoms.
  • R 22 is preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. Of these, an alkoxy group having 1 to 4 carbon atoms is more preferable.
  • R 21 and R 22 are alkenyl groups, the formulas (R1) to (R5)
  • a black dot in each formula represents a carbon atom in the ring structure.
  • a formula (R1) or a formula (R2) is more preferable.
  • the content of the compound in which R 21 and R 22 are alkenyl groups is preferably as small as possible, and preferably not contained.
  • Z 1 is preferably a single bond.
  • Z 1 is preferably —CH 2 CH 2 — or —CH 2 O—.
  • the fluorine atom of the compounds represented by the general formulas (N-01), (N-02), (N-03), (N-04) and (N-05) is replaced with a chlorine atom of the same halogen group. It may be done. However, the content of the compound substituted with a chlorine atom is preferably as small as possible, and is preferably not contained.
  • the hydrogen atom present on the ring of the compound represented by formula (N-01), (N-02), (N-03), (N-04) or (N-05) is a fluorine atom or chlorine. Although it may be substituted with an atom, a chlorine atom is not preferred.
  • the compounds represented by the general formulas (N-01), (N-02), (N-03), (N-04) and (N-05) have a negative ⁇ and an absolute value larger than 3. It is preferably a compound.
  • R 22 preferably represents an alkoxy group having 1 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms is particularly preferable.
  • the liquid crystal composition of the present invention includes, as the compound represented by the general formula (N-01), the general formula (N-01-1), the general formula (N-01-2) and the general formula (N-01-3). ) And the general formula (N-01-4)
  • R 21 represents the same meaning as described above, and R 23 independently represents an alkoxy group having 1 to 4 carbon atoms.
  • One kind of compound selected from the group of compounds represented by It is preferable to contain two or more kinds.
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, and a compound represented by the general formula (N-01-1) to the general formula (N-01-4). It is preferable to contain one or more compounds selected from the group.
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-01-1) and a general formula (N-01-4). It is preferable to contain a compound represented by
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-01-3) and a general formula (N-01-4). It is preferable to contain a compound represented by
  • the liquid crystal composition of the present invention includes, as the compound represented by the general formula (N-02), the general formula (N-02-1), the general formula (N-02-2), and the general formula (N-02- 3)
  • R 21 represents the same meaning as described above, and R 23 independently represents an alkoxy group having 1 to 4 carbon atoms.
  • One kind of compound selected from the group of compounds represented by It is preferable to contain two or more kinds.
  • the liquid crystal composition of the present invention preferably contains a polymerizable compound as the first component, a polymerizable compound as the second component, and a compound represented by the general formula (N-02-1).
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-02-1) and a general formula (N-02-3). It is preferable to contain a compound represented by
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-02-1) and a general formula (N-01-4). It is preferable to contain a compound represented by
  • the liquid crystal composition of the present invention has the general formula (N-03-1) as a compound represented by the general formula (N-03).
  • R 21 has the same meaning as described above, and R 23 represents an alkoxy group having 1 to 4 carbon atoms. It is preferable to contain one kind or two or more kinds of compounds.
  • the liquid crystal composition of the present invention preferably contains the polymerizable compound as the first component, the polymerizable compound as the second component, and the compound represented by the general formula (N-03-1).
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-03-1) and a general formula (N-01-4). It is preferable to contain a compound represented by
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-03-1) and a general formula (N-02-1). It is preferable to contain a compound represented by
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-03-1) and a general formula (N-01-4). It is preferable to contain the compound represented by the formula (1) and the compound represented by the general formula (N-02-1).
  • the liquid crystal composition of the present invention has the general formula (N-04-1) as a compound represented by the general formula (N-04).
  • R 21 has the same meaning as described above, and R 23 represents an alkoxy group having 1 to 4 carbon atoms. It is preferable to contain one kind or two or more kinds of compounds.
  • the liquid crystal composition of the present invention preferably contains the polymerizable compound as the first component, the polymerizable compound as the second component and the compound represented by the general formula (N-04-1) at the same time.
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-04-1) and a general formula (N-01-4). It is particularly preferable to simultaneously contain the compound represented by
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-04-1) and a general formula (N-01-4). It is particularly preferable to simultaneously contain the compound represented by and the compound represented by the general formula (N-02-1).
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-04-1) and a general formula (N-01-4). It is particularly preferable to simultaneously contain the compound represented by and the compound represented by the general formula (N-03-1).
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-04-1) and a general formula (N-02-1). It is particularly preferable to simultaneously contain the compound represented by and the compound represented by the general formula (N-03-1).
  • the liquid crystal composition of the present invention comprises a polymerizable compound as the first component, a polymerizable compound as the second component, a compound represented by the general formula (N-04-1) and a general formula (N-01-4). It is particularly preferable to simultaneously contain the compound represented by and the compound represented by the general formula (N-02-1) and the compound represented by the general formula (N-03-1).
  • the liquid crystal composition of the present invention includes, as the compound represented by the general formula (N-05), a compound selected from the compound group represented by the formulas (N-05-1) to (N-05-3). May be included.
  • the lower limit of the preferred content of the compound represented by the general formula (N-01) is 0%, 1%, 5%, or 10% with respect to the total amount of the liquid crystal composition of the present invention. , 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% Is.
  • the preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. And 15% and 10%.
  • the lower limit of the preferred content of the compound represented by the general formula (N-02) is 0%, 1%, 5%, or 10% with respect to the total amount of the liquid crystal composition of the present invention. , 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% Is.
  • the preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. And 15% and 10%.
  • the lower limit of the preferred content of the compound represented by formula (N-03) is 0%, 1%, 5%, or 10% with respect to the total amount of the liquid crystal composition of the present invention. , 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% Is.
  • the preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. And 15% and 10%.
  • the lower limit of the preferred content of the compound represented by formula (N-04) is 0%, 1%, 5%, or 10% with respect to the total amount of the liquid crystal composition of the present invention. , 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% Is.
  • the preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. And 15% and 10%.
  • the lower limit of the preferred content of the compound represented by formula (N-05) is 0%, 2%, 5%, or 8% with respect to the total amount of the liquid crystal composition of the present invention. Yes, 10%, 13%, 15%, 17%, 20%.
  • the preferable upper limit of the content is 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%.
  • the liquid crystal composition of the present invention may further contain one kind or two or more kinds of the compound represented by the general formula (N-06).
  • the lower limit of the preferred content of the compound represented by formula (N-06) is 0%, 2%, 5%, or 8% with respect to the total amount of the liquid crystal composition of the present invention. Yes, 10%, 13%, 15%, 17%, 20%.
  • the preferable upper limit of the content is 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%. And 5%.
  • the liquid crystal composition of the present invention includes the general formula (NU-01) to the general formula (NU-08)
  • R NU11, R NU12, R NU21, R NU22, R NU31, R NU32, R NU41, R NU42, R NU51, R NU52, R NU61, R NU62, R NU71, R NU72, R NU81 and R NU82 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms.
  • One or two or more non-adjacent —CH 2 — groups in the group are each independently —CH ⁇ CH—, —C ⁇ C—, —O—, —CO—, —COO— or —OCO. It may be substituted by-) and contains one or more compounds selected from the group of compounds represented by
  • R NU11, R NU12, R NU21, R NU22, R NU31, R NU32, R NU41, R NU42, R NU51, R NU52, R NU61, R NU62, R NU71, R NU72, R NU81 and R NU82 is preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms.
  • at least one R NU11 , R NU21 , R NU41 and R NU51 is preferably an alkenyl group having 2 to 3 carbon atoms, and is an alkenyl represented by the formula (R2). Groups are preferred.
  • the compound having an alkenyl group is preferably 30% or less, more preferably 25% or less, preferably 20% or less, preferably 15% or less, and 10% or less with respect to the total amount of the liquid crystal composition of the present invention. % Or less is preferable.
  • the compound having an alkenyl group is preferably 10% or less, preferably 5% or less, preferably 1% or less, and preferably not contained.
  • R NU11 , R NU21 , R NU31 , R NU41 , R NU51 , R NU61 , R NU71 , and R NU81 are particularly preferably an alkyl group having 1 to 5 carbon atoms
  • R NU12 , R NU22 , and R NU22 are particularly preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.
  • the liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-02).
  • the liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-03).
  • the liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-03) and a compound represented by the general formula (NU-04).
  • the liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-03) and a compound represented by the general formula (NU-05).
  • the liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-06).
  • the liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-07).
  • the liquid crystal composition of the present invention preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-08).
  • the liquid crystal composition of the present invention contains a compound represented by the general formula (NU-01), a compound represented by the general formula (NU-02) and a compound represented by the general formula (NU-04). Is more preferable.
  • the liquid crystal composition of the present invention contains a compound represented by the general formula (NU-01), a compound represented by the general formula (NU-03) and a compound represented by the general formula (NU-05). Is more preferable.
  • the liquid crystal composition of the present invention includes a compound represented by the general formula (NU-01), a compound represented by the general formula (NU-02), a compound represented by the general formula (NU-03) and a general formula (NU It is more preferable to contain a compound represented by NU-05).
  • the content of the compound represented by the general formula (NU-01) is preferably 1 to 60% by mass, more preferably 10 to 50% by mass, and further preferably 20 to 40% by mass. preferable.
  • the content of the compound represented by the general formula (NU-02) is preferably 1 to 40% by mass, more preferably 5 to 25% by mass, and further preferably 5 to 20% by mass. preferable.
  • the content of the compound represented by the general formula (NU-03) is preferably 1 to 20% by mass, more preferably 0 to 15% by mass, and further preferably 0 to 10% by mass. preferable.
  • the content of the compound represented by the general formula (NU-04) is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, and further preferably 3 to 10% by mass. preferable.
  • the content of the compound represented by the general formula (NU-05) is preferably 1 to 30% by mass, more preferably 1 to 20% by mass, and further preferably 3 to 20% by mass. preferable.
  • the content of the compound represented by the general formula (NU-06) is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, and further preferably 3 to 10% by mass. preferable.
  • the content of the compound represented by the general formula (NU-07) is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, and further preferably 3 to 10% by mass. preferable.
  • the content of the compound represented by the general formula (NU-08) is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, and further preferably 3 to 10% by mass. preferable.
  • the liquid crystal composition of the present invention may contain one kind or two or more kinds of compounds having positive dielectric anisotropy described in paragraphs 0236 to 0509 of Patent Document 4 (Patent No. 6233550).
  • composition of the present invention does not contain a compound having a structure in which oxygen atoms are bonded to each other such as a peracid (—CO—OO—) structure in the molecule.
  • the content of the compound having a carbonyl group is preferably 5% or less, and more preferably 3% or less with respect to the total mass of the composition. It is more preferably 1% or less, and most preferably substantially not contained.
  • the content of the compound in which the chlorine atom is substituted is preferably 15% or less, and more preferably 10% or less with respect to the total mass of the composition. % Or less, preferably 5% or less, more preferably 3% or less, and further preferably substantially not contained.
  • the content of the compound in which all the ring structures in the molecule are 6-membered rings is 80 relative to the total mass of the composition. % Or more, more preferably 90% or more, still more preferably 95% or more, and the composition is composed of only compounds in which all the ring structures in the molecule are all 6-membered rings. Most preferably.
  • the content of the compound having a cyclohexenylene group as a ring structure, and the content of the compound having a cyclohexenylene group to the total mass of the composition is preferably 10% or less, more preferably 8% or less, further preferably 5% or less, more preferably 3% or less, and further preferably substantially not contained.
  • the content of the compound having a 2-methylbenzene-1,4-diyl group in which a hydrogen atom may be replaced by a halogen in the molecule may be reduced. It is preferable that the content of the compound having the 2-methylbenzene-1,4-diyl group in the molecule is 10% or less, and preferably 8% or less, based on the total mass of the composition. It is more preferably 5% or less, more preferably 3% or less, and further preferably substantially not contained.
  • substantially free of means not including any substance that is unintentionally included.
  • the liquid crystal composition of the present invention may contain a normal nematic liquid crystal, a smectic liquid crystal, a cholesteric liquid crystal, an antioxidant, an ultraviolet absorber, a light stabilizer or an infrared absorber in addition to the above-mentioned compounds.
  • the liquid crystal composition of the present invention preferably contains an antioxidant so that the liquid crystal composition does not polymerize in the heat treatment which is one of the manufacturing steps of the liquid crystal display element.
  • an antioxidant When the antioxidant is not contained, the polymerization proceeds in the heat treatment before the UV irradiation step, and the desired orientation cannot be obtained.
  • antioxidant examples include hindered phenols represented by the general formula (H-1) to the general formula (H-4).
  • R H1's each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or 2 carbon atoms. Represents an alkenyl group having 1 to 10 carbon atoms or an alkenyloxy group having 2 to 10 carbon atoms. More specifically, R H1 is more preferably an alkyl group having 3 carbon atoms.
  • M H1 is an alkylene group having 4 to 10 carbon atoms (one or more —CH 2 — in the alkylene group is O-, -CO-, -COO-, -OCO- may be substituted), -OCH 2- , -CH 2 O-, -COO-, -OCO-, -CF 2 O-,-.
  • the liquid crystal composition of the present invention contains an antioxidant
  • its lower limit is preferably 10 mass ppm, 20 mass ppm is preferable, 50 mass ppm is preferable, and its upper limit is 10000 mass ppm, but 1000 mass ppm. Is preferable, 500 mass ppm is preferable, and 100 mass ppm is preferable.
  • the liquid crystal composition of the present invention has a nematic phase-isotropic liquid phase transition temperature (T NI ) of 60 ° C. to 120 ° C., more preferably 70 ° C. to 100 ° C., particularly preferably 70 ° C. to 85 ° C.
  • T NI nematic phase-isotropic liquid phase transition temperature
  • 60 degreeC or more is expressed as TNI being high.
  • T NI is preferably 70 to 80 ° C.
  • T NI is preferably 80 to 90 ° C.
  • outdoor display applications such as PID (Public Information Display)
  • T NI is 90 to 90 ° C. 110 ° C is preferred.
  • the liquid crystal composition of the present invention has a refractive index anisotropy ( ⁇ n) at 20 ° C. of 0.08 to 0.14, more preferably 0.09 to 0.13, and 0.09 to 0.12. Particularly preferred. More specifically, it is preferably 0.10 to 0.13 when it corresponds to a thin cell gap, and 0.08 to 0.10 when it corresponds to a thick cell gap.
  • the liquid crystal composition of the present invention particularly preferably has a refractive index anisotropy ( ⁇ n) at 20 ° C. of 0.098 to 0.118.
  • the liquid crystal composition of the present invention has a rotational viscosity ( ⁇ 1 ) at 20 ° C. of 50 to 160 mPa ⁇ s, preferably 55 to 160 mPa ⁇ s, and more preferably 60 to 160 mPa ⁇ s.
  • ⁇ 1 rotational viscosity
  • the liquid crystal composition of the present invention has a dielectric anisotropy ( ⁇ ) at 20 ° C. of -1.7 to -4.0, preferably -1.7 to -3.5, and from -1.8. -3.5 is more preferable, and -1.9 to -3.3 is more preferable.
  • the liquid crystal composition of the present invention contains a polymerizable compound as a first component and a polymerizable compound as a second component, and further contains the general formula (N-01), the general formula (N-02) and the general formula (N-03). ), A general formula (N-04), a general formula (N-05) and a general formula (N-06), and one or more compounds selected from the group of compounds represented by the general formula (NU -01) to (NU-08), it is preferable to contain one or more compounds selected from the group of compounds, and the upper limit of the total of these contents is 100% by mass and 99% by mass.
  • 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 %, 85% by mass, and 84% by mass are preferable, and
  • the lower limit of the total is 78% by mass, 80% by mass, 81% by mass, 83% by mass, 85% by mass, 86% by mass, 87% by mass, 88% by mass, 89% by mass, 90% by mass, 91% by mass, It is preferably 92% by mass, 93% by mass, 94% by mass, 95% by mass, 96% by mass, 97% by mass, 98% by mass, 99% by mass and 100% by mass.
  • the liquid crystal composition of the present invention contains a polymerizable compound as a first component and a polymerizable compound as a second component, and further contains the general formula (N-01), the general formula (N-02) and the general formula (N-03). ) And one or more compounds selected from the group of compounds represented by the general formula (N-04), and from the group of compounds represented by the general formulas (NU-01) to (NU-08) It is particularly preferable to contain one or more selected compounds, and the upper limit of the total of these contents is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96% by mass, 95% by mass.
  • the lower limit of the total of these contents is 78% by mass, 80% by mass , 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 It is preferably mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%, and 100 mass%.
  • the liquid crystal composition of the present invention can impart a sufficiently high polymerization rate and a sufficiently large pretilt angle.
  • the liquid crystal display device using the liquid crystal composition of the present invention has a small residual amount of the polymerizable compound in the liquid crystal display device after the polymerization, and is a high-definition PSA type or PSVA type liquid crystal display device such as 4K or 8K. It is possible to prevent or significantly suppress display defects such as IS. From the above, the production efficiency of a 4K or 8K high-definition PSA type or PSVA type liquid crystal display device can be remarkably improved, and the industrial utility value is very high.
  • the liquid crystal composition of the present invention is suitable for producing a PSA type or PSVA type liquid crystal display element, and also suitable for producing an NPS type liquid crystal display element. Further, it is also suitable for producing a PI-less type liquid crystal display element characterized by not having an alignment film.
  • the liquid crystal composition of the present invention is also suitable for a liquid crystal display element having no alignment film, that is, a mode commonly referred to as PI-less.
  • PI-less a mode commonly referred to as PI-less.
  • the liquid crystal composition of the present invention is useful for a liquid crystal display device for driving an active matrix, and can be used for liquid crystal display devices such as PSA, PSVA, PS-IPS, PS-FFS, and NPS.
  • the liquid crystal display element of the present invention includes a first substrate and a second substrate which are arranged to face each other, a common electrode provided on the first substrate or the second substrate, and the first substrate or the first substrate. It is preferable to have a pixel electrode provided on the second substrate and having a thin film transistor, and a liquid crystal layer containing a liquid crystal composition provided between the first substrate and the second substrate. If necessary, an alignment film for controlling the alignment direction of liquid crystal molecules may be provided on the facing surface side of at least one of the first substrate and / or the second substrate so as to come into contact with the liquid crystal layer.
  • a vertical alignment film, a horizontal alignment film, or the like can be appropriately selected according to the driving mode of the liquid crystal display element, and a rubbing alignment film (eg, polyimide) or a photo alignment film (decomposition type polyimide, etc.), etc.
  • a rubbing alignment film eg, polyimide
  • a photo alignment film decomposition type polyimide, etc.
  • the well-known alignment film can be used.
  • a color filter may be appropriately provided on the first substrate or the second substrate, and a color filter can be provided on the pixel electrode or the common electrode.
  • the two substrates of the liquid crystal cell used in the liquid crystal display element of the present invention can be made of a transparent transparent material such as glass or plastic, and one of them may be an opaque material such as silicon.
  • the transparent substrate having the transparent electrode layer can be obtained, for example, by sputtering indium tin oxide (ITO) on a transparent substrate such as a glass plate.
  • the color filter can be produced by, for example, a pigment dispersion method, a printing method, an electrodeposition method, a dyeing method, or the like.
  • the method for producing a color filter by the pigment dispersion method will be described as an example.
  • a curable colored composition for a color filter is applied on the transparent substrate, subjected to patterning treatment, and cured by heating or light irradiation. By performing this step for each of the three colors of red, green, and blue, a pixel portion for a color filter can be manufactured.
  • a pixel electrode provided with an active element such as a TFT, a thin film diode, a metal insulator and a metal specific resistance element may be provided on the substrate.
  • first substrate and the second substrate it is preferable to face the first substrate and the second substrate so that the common electrode and the pixel electrode layer are inside.
  • the distance between the first substrate and the second substrate may be adjusted via a spacer.
  • the polarizing axis of each polarizing plate can be adjusted so that the viewing angle and contrast are improved. Further, a retardation film for widening the viewing angle can also be used.
  • the spacer include glass particles, plastic particles, alumina particles, photoresist materials, and the like.
  • a usual vacuum injection method or ODF method can be used as a method for sandwiching the liquid crystal composition between the two substrates.
  • the polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention in order to obtain good alignment performance of the liquid crystal, it is desirable to polymerize at an appropriate polymerization rate, and therefore, the activity of an ultraviolet ray, an electron beam, etc.
  • a method of polymerizing by irradiating an energy ray singly or in combination or sequentially is preferable.
  • ultraviolet rays When ultraviolet rays are used, a polarized light source or a non-polarized light source may be used.
  • the polymerization is carried out in a state where the liquid crystal composition is sandwiched between two substrates, at least the substrate on the irradiation surface side must be provided with appropriate transparency for active energy rays.
  • the orientation state of the unpolymerized part is changed by changing conditions such as electric field, magnetic field or temperature, and further irradiation with active energy rays is performed. It is also possible to use a means of polymerizing the polymer.
  • a means of polymerizing the polymer In particular, when exposing to ultraviolet light, it is preferable to apply ultraviolet light while applying a DC electric field or an AC electric field to the liquid crystal composition.
  • the applied alternating electric field is preferably an alternating current having a frequency of 1 Hz to 10 kHz, more preferably a frequency of 60 Hz to 10 kHz, and the voltage is selected depending on the desired pretilt angle of the liquid crystal display element.
  • the pretilt angle of the liquid crystal display element can be controlled by the applied voltage.
  • IS occurs if the polymerizable compound remains unpolymerized after the device is manufactured.
  • the amount of the remaining polymerizable compound is preferably 100 ppm or less, more preferably 50 ppm or less, particularly preferably 20 ppm or less, particularly preferably the detection lower limit or less, or 0.
  • the temperature at the time of irradiation with active energy rays such as ultraviolet rays or electron rays used when polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention is not particularly limited.
  • active energy rays such as ultraviolet rays or electron rays used when polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention
  • it is preferably within a temperature range in which the liquid crystal state of the liquid crystal composition is maintained. That is, it is preferable to polymerize at 15 to 50 ° C.
  • a metal halide lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, or the like can be used as a lamp for generating ultraviolet rays, and an ultra-high-pressure UV lamp manufactured by USHIO and a fluorescent ultraviolet lamp manufactured by TOSHIBA are preferable.
  • an ultra-high-pressure UV lamp manufactured by USHIO and a fluorescent ultraviolet lamp manufactured by TOSHIBA are preferable.
  • the wavelength of the ultraviolet rays to be irradiated it is preferable to irradiate the ultraviolet rays in a wavelength range other than the absorption wavelength range of the liquid crystal composition, and it is preferable to use the ultraviolet rays after cutting the ultraviolet rays if necessary.
  • the intensity of ultraviolet rays to be applied is preferably 0.1 mW / cm 2 to 100 W / cm 2, and more preferably 2 mW / cm 2 to 50 W / cm 2 .
  • the amount of energy of the ultraviolet rays to be irradiated can be appropriately adjusted, but is preferably 10 mJ / cm 2 to 500 J / cm 2, and more preferably 100 mJ / cm 2 to 200 J / cm 2 .
  • T ni Nematic phase-isotropic liquid phase transition temperature (° C.) ⁇ n: refractive index anisotropy at 20 ° C ⁇ : viscosity at 20 ° C (mPa ⁇ s) ⁇ 1 : rotational viscosity at 20 ° C. (mPa ⁇ s) ⁇ : dielectric anisotropy at 20 ° C.
  • K 33 elastic constant at 20 ° C.
  • K 33 (pN) Manufacturing method and evaluation method of liquid crystal display element) (Evaluation of pretilt angle change amount) First, the pretilt angle of the liquid crystal display element was measured and used as the pretilt angle (initial).
  • pretilt angle was measured and used as the pretilt angle (after the test).
  • pretilt angle change amount absolute value of pretilt angle change
  • pretilt angle was measured using a pretilt angle measuring system (“OPTIPRO” manufactured by Shintech Co., Ltd.). Moreover, the magnitude of the applied voltage (30 V) is several times larger than the normal drive voltage, and this evaluation test is an acceleration test.
  • pretilt angle change amount is to 0 [°]
  • the liquid crystal cell containing the polymerizable compound was injected into the liquid crystal cell using a fluorescent UV lamp so that the illuminance measured under the condition of the central wavelength of 365 nm was 3.5 mW / cm 2, and the ultraviolet light was 120%.
  • a liquid crystal display element was obtained by irradiating for a minute (note that each characteristic value of the liquid crystal display element was evaluated using a liquid crystal display element prepared by a similar method).
  • the liquid crystal display device was disassembled to obtain an acetonitrile solution of an elution component containing a liquid crystal composition, a polymer and an unreacted polymerizable compound. This was analyzed by high performance liquid chromatography to measure the peak area of each component. The amount of the remaining polymerizable compound was determined from the peak area ratio of the liquid crystal compound as an index and the peak area of the unreacted polymerizable compound.
  • the residual amount of the polymerizable compound was determined from this value and the amount of the polymerizable compound initially added.
  • the detection limit of the residual amount of the polymerizable compound was 10 ppm. In this evaluation, the residual amount of 100 ppm was set as the allowable limit range of display defects. (Evaluation of voltage holding ratio) First, a liquid crystal composition containing a polymerizable compound was injected by a vacuum injection method into a liquid crystal cell having a cell gap of 3.5 ⁇ m and including a substrate with ITO having no polyimide alignment film. Next, after heating at 120 ° C.
  • Comparative Example 1 With respect to 100 parts by mass of the liquid crystal composition LC-1, 0.2 parts by mass of the compound represented by the formula (SAL-X1) and 0.4 parts by mass of the compound represented by the formula (SAL-X2), Comparative Example 1 was a liquid crystal composition containing a polymerizable compound to which 0.6 part by mass of the compound represented by the formula (RM-R1) was added.
  • Comparative Example 2 With respect to 100 parts by mass of the liquid crystal composition LC-1, 0.2 parts by mass of the compound represented by the formula (SAL-X1) and 0.4 parts by mass of the compound represented by the formula (SAL-X2), Comparative Example 2 was a liquid crystal composition containing a polymerizable compound containing 0.6 part by mass of the compound represented by the formula (RM-R2).
  • Example 1 With respect to 100 parts by mass of the liquid crystal composition LC-1, 0.2 parts by mass of the compound represented by the formula (SAL-X1) and 0.4 parts by mass of the compound represented by the formula (SAL-X2), Example 1 was a liquid crystal composition containing a polymerizable compound to which 0.6 part by mass of the compound represented by the formula (RM-11) was added.
  • Example 2 With respect to 100 parts by mass of the liquid crystal composition LC-1, 0.2 parts by mass of the compound represented by the formula (SAL-X1) and 0.4 parts by mass of the compound represented by the formula (SAL-X2), Example 2 was a liquid crystal composition containing a polymerizable compound to which 0.6 part by mass of the compound represented by the formula (RM-3) was added.
  • Example 3 With respect to 100 parts by mass of the liquid crystal composition LC-1, 0.2 parts by mass of the compound represented by the formula (SAL-X1) and 0.4 parts by mass of the compound represented by the formula (SAL-X2), Example 3 was a liquid crystal composition containing a polymerizable compound to which 0.6 part by mass of the compound represented by the formula (RM-4) was added.
  • Example 4 A liquid crystal composition containing a polymerizable compound containing 0.3 part by mass of the compound represented by the formula (RM-1) and 0.3 part by mass of the compound represented by the formula (RM-11) was prepared.
  • Example 5 A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 part by mass of the compound represented by the formula (RM-1) and 0.3 part by mass of the compound represented by the formula (RM-3) was used.
  • the liquid crystal composition of the present invention has a sufficiently high voltage holding ratio, is less likely to cause a display defect due to a change in the pretilt angle, and is free from deposition of a polymerizable compound.
  • Comparative Examples 3 and 4, Examples 6 to 10 With respect to 100 parts by mass of the liquid crystal composition LC-2, 0.4 parts by mass of the compound represented by the formula (SAL-X2) and 0.5 parts by mass of the compound represented by the formula (SAL-X3), Comparative Example 3 was a liquid crystal composition containing a polymerizable compound to which 0.6 part by mass of the compound represented by the formula (RM-R3) was added.
  • a liquid crystal composition containing a polymerizable compound containing 0.6 part by mass of the compound represented by the formula (RM-R3) was set as Comparative Example 4.
  • Example 6 was a liquid crystal composition containing a polymerizable compound to which 0.6 part by mass of the compound represented by the formula (RM-25) was added.
  • Example 7 was a liquid crystal composition containing a polymerizable compound to which 0.6 part by mass of the compound represented by the formula (RM-28) was added.
  • Example 8 was a liquid crystal composition containing a polymerizable compound to which 0.6 part by mass of the compound represented by the formula (RM-23) was added.
  • Example 9 was a liquid crystal composition containing a polymerizable compound to which 0.6 part by mass of the compound represented by the formula (RM-33) was added.
  • Example 10 A liquid crystal composition containing a polymerizable compound to which 0.3 part by mass of the compound represented by the formula (RM-25) and 0.3 part by mass of the compound represented by the formula (RM-28) were added.
  • Example 11 A liquid crystal composition containing a polymerizable compound obtained by adding 0.3 part by mass of the compound represented by the formula (RM-25) and 0.3 part by mass of the compound represented by the formula (RM-23) was used.

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Abstract

La présente invention vise à fournir : une composition de cristaux liquides contenant un composé polymérisable, la composition conservant la force de commande d'alignement intacte pour aligner verticalement les molécules de cristaux liquides, provoquant très peu ou pas de défaillances d'affichage dues à un changement d'angle de pré-inclinaison, et ayant un rapport de maintien de tension élevé ; et un élément d'affichage à cristaux liquides comprenant la composition de cristaux liquides. La composition de cristaux liquides de la présente invention contient un composé polymérisable spécifique. La présente invention concerne par conséquent la composition de cristaux liquides et l'élément d'affichage à cristaux liquides comprenant ladite composition de cristaux liquides.
PCT/JP2019/037807 2018-10-11 2019-09-26 Composition de cristaux liquides polymérisable et élément d'affichage à cristaux liquides WO2020075509A1 (fr)

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